Guest Stars Nick Robinson as Robert Todd Lincoln Wanda Sykes as Shirley Chisholm Kym Whitley as Florynce Kennedy Colton Dunn as Conrad Chisholm Ike Barinholtz as General Ulysses S. Grant Zahn McClarnon as Private Mingoes Marla Gibbs as Ruby Seale Tyler James Williams as Private Mason Dixon Tim Baltz as Lieutenant Henry Honeybeard Jason Acuña as Russian Craig Cackowski as Joseph Stalin Wanda Sykes as Harriet Tubman Chris Pontius as Russian Assassin Preston Lacy as Russian Noble James Adomian as President Richard Nixon George Wallace as Governor George Wallace Andrew Rannells as Sergei Nick Kroll as Galileo Tim Bagley as Doctor Dan Bakkedahl as Winston Churchill Christopher Thornton as President Franklin Roosevelt Brandon Kyle Goodman as Clay Co Starring Katherine LaVeaux as TBD Jon Daly as Glenn Scott MacArthur as Fleetus Edgar Blackmon as Audience Member Eric Nenninger as TBD David Stassen as Sitcom Director